This invention relates to the catalytic cyano-alkylation or amido-alkylation of hydroxyaromatic reactants and to compounds made thereby.
Compounds containing terminal amide or nitrile moieties are useful as precursors to carboxylic acids. Several routes to amido-alkylated hydroxyaromatic compounds are known. For example, a three-step method of synthesizing a di(amido-methylated)hydroquinone derivative is disclosed in Chemical Abstracts, Vol. 64, 17566e (1966). This three-step method involves reacting hydroquinone with chloroacetic acid, reacting the resulting carboxylic acid with thionyl chloride, and then reacting the next resulting acid chloride with ammonia to get p-phenylenedioxy diacetamide. It is also known to convert hydroquinone to a diester, which is then subjected to aminolysis to yield p-phenylenedioxy diacetamide. Diss. Pharm. Pharmacol., Vol. 20, No. 6, 589-597 (1968).
U.S. Pat. No. 3,716,583 discloses, among other things, a non-catalytic method of forming amido-alkylated bisphenolic derivatives. The first step requires reacting a bisphenolic compound with an alkaline agent to form an alkaline salt. Then, an .alpha.-halogenated aliphatic acid derivative is added to start a condensation reaction, thereby forming an arylenedioxy dialkyleneamide.
Arylenedioxy dialkylenenitriles have also been prepared in the past. U.S. Pat. No. 4,061,777 discloses the non-catalytic reaction of .alpha.-chloroacetonitrile with substituted phenols to get the corresponding phenoxyacetonitrile. Similarly, alcohols were reacted with .alpha.-chloroacetonitrile in the presence of KOH and benzene to give alkoxynitriles. Chemical Abstracts, Vol. 85, 159369d (1976). Arylenedioxy dialkylenenitriles are also available via Michael addition of acrylonitrile to hydroxyaromatic compounds, however, yields are modest.
Heretofore, a high yield process for the catalytic monophasic amido-alkylation or cyano-alkylation of hydroxyaromatic compounds has not been disclosed.